C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
2-(3-Cl-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.57 s_N Param.: 0.53	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(4-Br-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.62 s_N Param.: 0.53	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(4-CN-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 23.64 s_N Param.: 0.65	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(4-NO2-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 20.00 s_N Param.: 0.71	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate	dichloromethane	N Param.: 1.72 s_N Param.: 1.24	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO)	DMSO	N Param.: 30.82 s_N Param.: 0.41	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
2-(bis(tert-butyldimethylsiloxy)amino)propene	dichloromethane	N Param.: 4.23 s_N Param.: 0.93	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
2-(bis(trimethylsiloxy)amino)propene	dichloromethane	N Param.: 4.76 s_N Param.: 0.86	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
2-(diethylamino)-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)	DMSO	N Param.: 27.45 s_N Param.: 0.38	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
2-(pentamethyldisilyl)propene	dichloromethane	N Param.: -0.26 s_N Param.: 0.95	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
2-(pyrid-4-yl)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 23.27 s_N Param.: 0.70	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 27.77 s_N Param.: 0.47	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
2-(tert.butyldimethylsiloxy)propene	dichloromethane	N Param.: 5.58 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tributylsilyl)furan	dichloromethane	N Param.: 2.37 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tributylstannyl)furan	dichloromethane	N Param.: 3.63 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tributylstannyl)thiophene	dichloromethane	N Param.: 1.53 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(triethylsilyl)furan	dichloromethane	N Param.: 2.20 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(triisopropylsiloxy)propene	dichloromethane	N Param.: 5.38 s_N Param.: 0.85	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran	dichloromethane	N Param.: 10.61 s_N Param.: 0.86	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN)	MeCN	N Param.: 10.52 s_N Param.: 0.78	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
2-(trimethylsiloxy)buta-1,3-diene	dichloromethane	N Param.: 4.83 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(trimethylsiloxy)furan	dichloromethane	N Param.: 7.22 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(trimethylsiloxy)propene	dichloromethane	N Param.: 5.41 s_N Param.: 0.91	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(trimethylsilyl)furan	dichloromethane	N Param.: 2.16 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(trimethylsilyl)propene	dichloromethane	N Param.: -1.46 s_N Param.: 1.05	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
2-(trimethylsilyl)thiophene	dichloromethane	N Param.: -0.80 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(triphenylsiloxy)propene	dichloromethane	N Param.: 4.46 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tris(pentafluorophenyl)siloxy)-propene	dichloromethane	N Param.: 0.58 s_N Param.: 0.91	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
2-(tris(trimethylsilyl)siloxy)propene	dichloromethane	N Param.: 6.04 s_N Param.: 0.82	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
2-(tris(trimethylsilyl)silyl)propene	dichloromethane	N Param.: -0.31 s_N Param.: 0.99	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
2-chloro-1,3-diethoxy-1,3-dioxopropan-2-ide (in DMSO)	DMSO	N Param.: 18.19 s_N Param.: 0.74	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
2-chloropropene	dichloromethane	N Param.: -3.65 s_N Param.: 1.97	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
2-cyclopropylpropene	dichloromethane	N Param.: 2.60 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-diazo-1-benzosuberone	dichloromethane	N Param.: 2.72 s_N Param.: 0.96	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazo-1-tetralone	dichloromethane	N Param.: 3.51 s_N Param.: 0.86	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazobenzothiophen-3(2H)-one	dichloromethane	N Param.: 0.40 s_N Param.: 0.93	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazocyclohexanone	dichloromethane	N Param.: 3.44 s_N Param.: 0.83	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazoindan-1-one	dichloromethane	N Param.: 5.61 s_N Param.: 0.65	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazoindandione	dichloromethane	N Param.: 0.16 s_N Param.: 0.86	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-ethoxy-1-fluoro-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)	DMSO	N Param.: 20.51 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
2-ethoxy-1-methoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)	DMSO	N Param.: 19.15 s_N Param.: 0.59	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
2-ethoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)	DMSO	N Param.: 18.81 s_N Param.: 0.59	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)	DMSO	N Param.: 26.71 s_N Param.: 0.37	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
2-fluoro-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)	DMSO	N Param.: 19.03 s_N Param.: 0.58	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
2-methoxy-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)	DMSO	N Param.: 17.36 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
2-methyl-1-(trimethylsiloxy)propen	dichloromethane	N Param.: 3.94 s_N Param.: 1.00	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-methyl-but-1-ene	dichloromethane	N Param.: 1.00 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-methyl-but-2-ene	dichloromethane	N Param.: 0.65 s_N Param.: 1.17	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-methyl-buta-1,3-diene (isoprene)	dichloromethane	N Param.: 1.10 s_N Param.: 0.98	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-methyl-pent-1-ene	dichloromethane	N Param.: 0.84 s_N Param.: 1.06	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b